Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H6N4O2 |
| Molecular Weight | 166.1374 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C=NC2=C1C(=O)NC(=O)N2
InChI
InChIKey=PFWLFWPASULGAN-UHFFFAOYSA-N
InChI=1S/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12)
7-Methylxanthine is a methyl derivative of xanthine, found occasionally in human urine. 7-Methylxanthine is one of the purine components in urinary calculi. 7-methylxanthine (7-MX) is a metabolite of caffeine and theobromine, and has been shown to have low toxicity and no carcinogenic effects. 7-MX is known as a non-selective adenosine antagonist and has been shown to work against myopia. 7-MX has little effect on the proliferation or apoptosis of human RPE cells; however, 7-MX disturbs the proportion of cells in the G1 stage and inhibits the expression of ADORA1, ADORA2A, and ADORA2B in short-term treatment. 7-MX has been confirmed to reduce the severity of myopia and eye elongation induced by forming deprivation in guinea pigs and to counteract the thinning of the posterior sclera and of collagen fibrils induced by form deprivation. A clinical trial showed that 7-MX reduced eye elongation and myopia progression in childhood myopia.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Use of novel solid-phase extraction sorbent materials for high-performance liquid chromatography quantitation of caffeine metabolism products methylxanthines and methyluric acids in samples of biological origin. | 2001 Aug 15 |
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| Caffeine metabolism before and after liver transplantation. | 2001 Feb |
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| Determination of urinary methylated purine pattern by high-performance liquid chromatography. | 2001 Feb 10 |
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| Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis. | 2001 Jan |
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| Group I aptazymes as genetic regulatory switches. | 2002 Dec 4 |
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| Differences in caffeine and paraxanthine metabolism between human and murine CYP1A2. | 2002 Jun 15 |
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| Identification of N1-methyl-2-pyridone-5-carboxamide and N1-methyl-4-pyridone-5-carboxamide as components in urine extracts of individuals consuming coffee. | 2002 Oct 15 |
|
| Isolation of a new dual-functional caffeine synthase gene encoding an enzyme for the conversion of 7-methylxanthine to caffeine from coffee (Coffea arabica L.). | 2003 Jan 16 |
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| Acid-base properties of xanthosine 5'-monophosphate (XMP) and of some related nucleobase derivatives in aqueous solution: micro acidity constant evaluations of the (N1)H versus the (N3)H deprotonation ambiguity. | 2004 Oct 11 |
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| Degradation kinetics of caffeine and related methylxanthines by induced cells of Pseudomonas sp. | 2007 Jul |
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| Systemic 7-methylxanthine in retarding axial eye growth and myopia progression: a 36-month pilot study. | 2008 Dec |
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| Distribution of adenosine receptors in human sclera fibroblasts. | 2008 Mar 14 |
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| Non-standard base pairing and stacked structures in methyl xanthine clusters. | 2008 May 21 |
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| Altered expression of the caffeine synthase gene in a naturally caffeine-free mutant of Coffea arabica. | 2009 Oct |
|
| Carotenoids in clams, Ruditapes philippinarum and Meretrix petechialis. | 2010 May 12 |
Sample Use Guides
During a 12-months placebo-controlled trial, participants received one tablet every morning. The tablets had a diameter of 12 mm and a thickness of 3 mm. Active tablets contained 400 mg 7-MX. The peak serum concentration after an oral dose of 400 mg 7-MX in adults is around 20 umol/l with a half-life of 200 min.
Route of Administration:
Oral
To observe the growth of cells treated with 7-MX, primary human RPE cells were incubated with different concentrations (from 1 nmol/l to 1 mmol/l) of 7-MX. No statistically significantly growth alteration was noted at 24, 72, and 96 h. A slightly decreased cell proliferation rate was seen with 100 umol/l 7-MX at 48 h, but without statistically significant differences compared to the other concentrations. To observe the effects of 7-MX on the mRNA levels of ADORs, RPE cells were cultured with 10 umol/l 7-MX for 24, 48, and 72 h.
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68374
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E9M81NJM6G
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552-62-5
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DTXSID60203696
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48991
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7861
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209-019-0
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PARENT (METABOLITE)
SUBSTANCE RECORD
